[6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile → [6-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinyl]acetonitrile

HRID 2401223ノート

反応式

HRID 2401223 の反応式
CS([C:4]1[N:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=1)=O.[F:13][C:14]([F:27])([F:26])[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[C:21]([CH2:23][NH2:24])[CH:22]=[C:17]2[CH:16]=1>C(O)(C)C.C(#N)C.CS(C)=O>[F:27][C:14]([F:13])([F:26])[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[C:21]([CH2:23][NH:24][C:4]3[N:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=3)[CH:22]=[C:17]2[CH:16]=1

参加物

6

反応物 2

HCID 67111377[6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile2 回HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2 回

生成物 1

HCID 51355873[6-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinyl]acetonitrile収率 8.4%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A mixture of [6-(methylsulfinyl)-4-pyrimidinyl]acetonitrile (Intermediate 16, 150 mg, 0.828 mmol) and 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 178 mg, 0.828 mmol) in isopropanol (7 mL) was stirred and heated at 80° C. overnight. The reaction mixture was cooled to room temperature and condensed. This solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (2.7 mL) and purified by MDAP (3 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure. The solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (1.8 mL) and purified again by MDAP (2 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure to give the title compound as a solid (23 mg);

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customcondensed
  3. custompurified by MDAP (3 injections)
  4. additionFractions containing the suspected product
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (1.8 mL)
  7. custompurified again by MDAP (2 injections)
  8. additionFractions containing the suspected product
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9d72a881b07642888a97df947162342b
出典データセット
uspto-grants-2014_08
特許番号
US08796283B2

反応ノート

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